Just a couple days ago I lost my car key, without having a spare one. What's worse, I know the key was picked up by some one living by, which means I couldn't leave car lock unchanged. This single one mistake cost me:

1. $300 - called Locksmith to open the door and make a programmed key, and
2. $500 - drove to Toyota dealership, had them change door locks and reseed my key,

totaling 800 bucks, which did upset me and depress me for quite a few days. I felt angry with my own carelessness just by thinking of how many stuff I could buy with 800 bucks as a frugal person.

What's a mistake/fault you ever made that indeed hurt your wallet? Legend has it that others' bitterness could make a sad one feel happier

Edit: Thanks for all replies:) A lot brought up their opportunity costs. Well, I'd not count these as mistakes. Otherwise, my biggest mistake would be not borrowing as much money as possible, selling all my properties, and all-in all I had to Bitcoin when it's dirt cheap

Last edited by bo105954027 on Wed Sep 19, 2018 1:03 pm, edited 2 times in total.

Just a couple days ago I lost my car key, without having a spare one. What's worse, I know the key was picked up by some one living by, which means I couldn't leave car lock unchanged. This single one mistake cost me:

1. $300 - called Locksmith to open the door and make a programmed key, and
2. $500 - drove to Toyota dealership, had them change door locks and reseed my key,

totaling 800 bucks, which did upset me and depress me for quite a few days. I felt angry with my own carelessness just by thinking of how many stuff I could buy with 800 bucks as a frugal person.

What's an mistake/fault you ever made that indeed hurt your wallet? Legend has it that others' bitterness could me an sad person feel happier

If this is your most expensive mistake, then you have been extremely fortunate!

Sure, $800 (plus the time and aggravation) is enough to make one sad, and probably quite annoyed with one's self, etc., but still... put it in perspective.
Next year, or in a few years, will the financial effects still be felt?
By retirement?

I’m only 23 so there haven’t been that many mistakes (yet), but my biggest mistake so far was going to college. I went to college for 2 years right after high school and quit with no degree and about $11K in student loan debt which I plan to have paid off in the next couple years. Looking back on it, there was no point in going to college as my career does not require a degree. On the other hand, I may not be where I am today if I hadn’t gone to college so it was probably for the best in the long run.

Marriage was my most expensive mistake in financial terms. However, I made out relatively lightly (ex-spouse made close to what I made) so it was a low six figure cost overall (between asset transfers and divorce costs). That said I got my son out of it and I think going through a marriage was unfortunately necessary for me to learn how I truly wanted to live my life. So my return on that "loss" in non-financial terms is excellent. Even if I could go back in time and change things I would pretty much do it again the same way (perhaps divorce a bit sooner though).

Just a couple days ago I lost my car key, without having a spare one. What's worse, I know the key was picked up by some one living by, which means I couldn't leave car lock unchanged. This single one mistake cost me:

1. $300 - called Locksmith to open the door and make a programmed key, and
2. $500 - drove to Toyota dealership, had them change door locks and reseed my key,

totaling 800 bucks, which did upset me and depress me for quite a few days. I felt angry with my own carelessness just by thinking of how many stuff I could buy with 800 bucks as a frugal person.

What's an mistake/fault you ever made that indeed hurt your wallet? Legend has it that others' bitterness could me an sad person feel happier

ED.......WARD.......JONES. Cost me about 100k. Though I did have a foolish marriage about 51 years ago. Didn't have much money then, so didn't cost too much.

My most expensive investment mistake was to use a financial planner, who was a friend. He invested my funds in load funds and a single premium life insurance company. The insurance company went into bankruptcy. That was the wakeup moment for me. I then read John Bogle's book Common Sense on Mutual funds and fired my FP. Thank you Mr. Bogle for your great book and insight.

Bought a new custom $100,000 27' SeaSport Seamaster set up as a dive boat for SE Alaska together with a friend of mine. We had some good adventures on it and sold it a few years later after we both got married for perhaps a $40,000 loss considering all we had in it.

Bought put options on Fannie Mae because it was "obvious" there was a housing bubble, and the stock market takes into account all information very quickly, right? Unfortunately I was 2 years too early on that bet and lost $50K. That was my lesson to stop speculating, because even when you are right about what's going to happen, you have to get the timing right too.

When I was fairly new to investing my older brother took me out for a birthday breakfast. We discussed investing at some point, and I went home and made some changes. Eventually, I calculated that those changes cost me $30,000 before I reversed them. It was then I realized that my brother, who I had grown up to admire, might not be very smart at investing.
Interestingly, I’m retired now. He never listened to my advice and is still working.

Followed by not not accepting the sunk costs earlier and getting out of either earlier.

Now life is different and I’m in a different “job” of running the family business. I sell landscape supplies. Or, as my employees say, I’m a dirt farmer.

To those that hate their jobs: get out now. Don’t regret the sunk costs. They’re gone. Go and live a different life while you can. You think life will be worse if you quit the career you chose but hate. Or that your family will be shocked/disappointed/let down, etc. Or that the money won’t be as good. Or that you should just suck it up. Or that you’ll be making an intergalactic mistake. I thought so too.

But my life is so much better now in every way I can’t believe it. I’d do it again even if the money wasn’t as good as it is now.

I haven’t practiced law in years and don’t miss it. The last time I used my law license was a year or two ago when I used it to scrape ice off a rental car windshield outside a hotel in the middle of nowhere Utah early one morning on the way to my home in Colorado. No one was at the front desk to borrow an ice scraper at that time of morning, and I didn’t want to screw up the credit card, because that’s more valuable to me these days. I knew that law license would come in handy one day . . .

I would have kept the locks the same and worried about theft once it happened. I am assuming the car is insured? Odds are nothing would have happened and I would be $500 richer.

I grew up in a lock shop and if someone wants to steal your toyota, they don't need a key. I always make sure to have spare keys at the house and usually an extra key in my travel luggage in case I lose my primary. My car doesn't have anything valuable enough in it to risk jail time.

I hold index funds because I do not overestimate my ability to pick stocks OR stock pickers.

• Paid Financial Planner about $1300/month for almost 2 years.
• Bought a $1,500 website domain by mistake. (Clicked too fast and just was trying to finish the transaction. Later sold it, though)
• Own a small company, "C" Corp....the tax man double taxes me for the last 20 years. Just cut a check for $29,000 in taxes for last fiscal year. I hate the tax man.
• Own a few rental houses. Let a tenant get about $1500 back before I realized he wasn't going to pay. He never did. Now, on day 6 of the month, if I don't have rent in hand, I start the eviction process on my tenants. No excuses...I've heard them all and don't really care.

Just a couple days ago I lost my car key, without having a spare one. What's worse, I know the key was picked up by some one living by, which means I couldn't leave car lock unchanged. This single one mistake cost me:

1. $300 - called Locksmith to open the door and make a programmed key, and
2. $500 - drove to Toyota dealership, had them change door locks and reseed my key,

totaling 800 bucks, which did upset me and depress me for quite a few days. I felt angry with my own carelessness just by thinking of how many stuff I could buy with 800 bucks as a frugal person.

What's an mistake/fault you ever made that indeed hurt your wallet? Legend has it that others' bitterness could me an sad person feel happier

If this is your most expensive mistake, then you have been extremely fortunate!

Sure, $800 (plus the time and aggravation) is enough to make one sad, and probably quite annoyed with one's self, etc., but still... put it in perspective.
Next year, or in a few years, will the financial effects still be felt?
By retirement?

RM

Or very young.

Good luck.

"The stock market [fluctuation], therefore, is noise. A giant distraction from the business of investing.” |
-Jack Bogle

Lots of little ones I learned from but this was the most recent: $3,000 deposit to special order a BMW with an estimated 3 month build time. Cancelled the deal 2 months later as circumstances changed (I relocated closer to children). Asked for the deposit back, they said no, I moved on.

Last edited by Gort on Tue Sep 18, 2018 6:19 pm, edited 2 times in total.

Probably not my most expensive mistake, but certainly the one I remember the most

Got laid off from my engineering job and instead of paying my neighbor to cut my grass (he was in the mowing business and did a brilliant job once a month for $25), I decided I would save money and do it myself. Moved my car out of the driveway, parked it on the street, started mowing the front grass - hit a stone with the mower, and the stone flew right through the passenger window of my Toyota. Cost me $200 to repair and 2 hours to clean up all the tiny tiny bits of glass.

For twenty five years, starting with a mid 5 figure 401K that grew to a mid 6 figure 401K, thinking that an appropriate asset allocation to spread market risk should equally weight stocks, bonds and cash (money market). Even changing my monthly contributions from time to time to maintain that allocation.

I've never had the nerve to try to figure out how much that cost me. I only saw the light when I retired, converted it all to cash, and moved it to a Vanguard IRA and discovered the Bogleheads forum.

Going in hardware instead of software.
Not going to large successful company when I had an offer many years ago.
My wife going to dentistry not medicine.
Not starting earlier and not putting enough effort into the admission process in grad school.

Of course these were expensive, but not necessarily mistakes. Wrong decision early in life have the tendency to compound to huge values. Easily millions.

There's something to be said about sunk costs.
But there's also something to be said about mistakes early in life compounding early.

Here's one from the past few months: New house. A/C wasn't working. Spent $800 to fix duct work in the attic. A/C still wasn't working. Spent $600 to fix refrigerant levels (overchaged). HVAC failed completely. Finally wised up and called my home warranty. I avoided another $400 bill and just paid the $100 deductible.

This past weekend, I decided to model out my buy vs rent decision. I will likely never break even.

Worst mistake: Rejecting the home inspector recommended by a trustworthy expert, in favor of one who had a really interesting and persuasive website.

Near Miss: Almost overfunding my individual 401(k). Withdrew the excess on the last possible day. I believe the penalty would have been double tax (the contribution is not deductible, and is taxed when withdrawn). It was a compound mistake, because that tax year I fully funded a 403(b) but not my 457, so if I had simply put more in the 457 and less in the 403(b), I would have had space in my I401(k).

My most expensive mistake was not realizing I should be very careful which dentist did my root canal. My general dentist did an incomplete job that promptly became painlessly infected and nearly fatal in the years before we identified the cause. Health insurance paid most of the $800k but I had to pay a lot, couldn't work for over a year, endured numerous ER visits and procedures, extremely unpleasant medications, several surgeries, and a decade later still depend on frightfully expensive drugs and regularly see six top-notch specialist MDs (plus an awesome, exceptional dentist).

My most expensive mistake was not realizing I should be very careful which dentist did my root canal. My general dentist did an incomplete job that promptly became painlessly infected and nearly fatal in the years before we identified the cause. Health insurance paid most of the $800k but I had to pay a lot, couldn't work for over a year, endured numerous ER visits and procedures, extremely unpleasant medications, several surgeries, and a decade later still depend on frightfully expensive drugs and regularly see six top-notch specialist MDs (plus an awesome, exceptional dentist).

Said some nice things to Paypal staff (including a younger Elon Musk, I am pretty sure, but he wasn't famous in 2001), and got a call from them asking if I'd like to invest in the IPO in their "friends and family" program. I declined, like a chump.

Example 2: was giving a panel in a room filled with excited fans who were eager to buy the Nintendo Wii before it came out. You could cut the energy in the room with a knife. Did I buy Nintendo stock the next day? Of course not.

Bought a new custom $100,000 27' SeaSport Seamaster set up as a dive boat for SE Alaska together with a friend of mine. We had some good adventures on it and sold it a few years later after we both got married for perhaps a $40,000 loss considering all we had in it.

The two happiest days in a boat owners life are the day he buys it and the day he sells it. I know the feeling.

In 2012 my wife and I started following Dave Ramsey’s Baby Steps. It's still one of the best things we’ve ever done. We didn’t have much debt at the time, but it helped us save like never before and eventually reach our retirement savings goal. However, we should have stopped reading Dave’s book before the chapter on investments. We followed his advice and hired one of his Endorsed Local Providers (ELP’s) to invest our retirement savings. What we got was a mess of actively managed mutual funds with high fees including front-end and back-end loads. His ELP may have had the “heart of a teacher,” but I believe his true motivation was that of a salesman only interested in lining his own pockets. To use Dave Ramsey’s own words, we paid a large “stupid tax” because we didn’t do our homework first and we didn’t understand what we were buying. Thankfully there’s a happy ending. Within a few months, I found a video online of Jack Bogle talking about low-cost index funds. I bought Jack’s Little Book of Common Sense Investing and within a few weeks we fired our salesman/broker, sold everything in our tax-deferred accounts and moved our savings to Vanguard.